Synthesis and biological evaluation of derivatives of 2-{2-fluoro-4-[(2- oxocyclopentyl)methyl]phenyl}propanoic acid: Nonsteroidal anti-inflammatory drugs with low gastric ulcerogenic activity

Naoki Yamakawa; Shintaro Suemasu; Yoshinari Okamoto; Ken Ichiro Tanaka; Tomoaki Ishihara; Teita Asano; Keishi Miyata; Masami Otsuka; Tohru Mizushima

doi:10.1021/jm300049g

Synthesis and biological evaluation of derivatives of 2-{2-fluoro-4-[(2- oxocyclopentyl)methyl]phenyl}propanoic acid: Nonsteroidal anti-inflammatory drugs with low gastric ulcerogenic activity

Naoki Yamakawa, Shintaro Suemasu, Yoshinari Okamoto, Ken Ichiro Tanaka, Tomoaki Ishihara, Teita Asano, Keishi Miyata, Masami Otsuka, Tohru Mizushima

Research output: Contribution to journal › Article › peer-review

23 Citations (Scopus)

Abstract

We previously reported that 2-fluoroloxoprofen has lower gastric ulcerogenic activity than loxoprofen, a nonsteroidal anti-inflammatory drug (NSAID) without selectivity for COX-2. We synthesized derivatives of 2-fluoroloxoprofen and studied their properties. Compared to 2-fluoroloxoprofen, one derivative, 11a, exhibited higher anti-inflammatory activity and an equivalent ulcerogenic effect. These results suggest that 11a could be therapeutically beneficial for use as an NSAID.

Original language	English
Pages (from-to)	5143-5150
Number of pages	8
Journal	Journal of Medicinal Chemistry
Volume	55
Issue number	11
DOIs	https://doi.org/10.1021/jm300049g
Publication status	Published - 2012 Jun 14

ASJC Scopus subject areas

Molecular Medicine
Drug Discovery

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Yamakawa, N., Suemasu, S., Okamoto, Y., Tanaka, K. I., Ishihara, T., Asano, T., Miyata, K., Otsuka, M., & Mizushima, T. (2012). Synthesis and biological evaluation of derivatives of 2-{2-fluoro-4-[(2- oxocyclopentyl)methyl]phenyl}propanoic acid: Nonsteroidal anti-inflammatory drugs with low gastric ulcerogenic activity. Journal of Medicinal Chemistry, 55(11), 5143-5150. https://doi.org/10.1021/jm300049g

Synthesis and biological evaluation of derivatives of 2-{2-fluoro-4-[(2- oxocyclopentyl)methyl]phenyl}propanoic acid : Nonsteroidal anti-inflammatory drugs with low gastric ulcerogenic activity. / Yamakawa, Naoki; Suemasu, Shintaro; Okamoto, Yoshinari et al.

In: Journal of Medicinal Chemistry, Vol. 55, No. 11, 14.06.2012, p. 5143-5150.

Research output: Contribution to journal › Article › peer-review

Yamakawa, N, Suemasu, S, Okamoto, Y, Tanaka, KI, Ishihara, T, Asano, T, Miyata, K, Otsuka, M & Mizushima, T 2012, 'Synthesis and biological evaluation of derivatives of 2-{2-fluoro-4-[(2- oxocyclopentyl)methyl]phenyl}propanoic acid: Nonsteroidal anti-inflammatory drugs with low gastric ulcerogenic activity', Journal of Medicinal Chemistry, vol. 55, no. 11, pp. 5143-5150. https://doi.org/10.1021/jm300049g

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abstract = "We previously reported that 2-fluoroloxoprofen has lower gastric ulcerogenic activity than loxoprofen, a nonsteroidal anti-inflammatory drug (NSAID) without selectivity for COX-2. We synthesized derivatives of 2-fluoroloxoprofen and studied their properties. Compared to 2-fluoroloxoprofen, one derivative, 11a, exhibited higher anti-inflammatory activity and an equivalent ulcerogenic effect. These results suggest that 11a could be therapeutically beneficial for use as an NSAID.",

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Synthesis and biological evaluation of derivatives of 2-{2-fluoro-4-[(2- oxocyclopentyl)methyl]phenyl}propanoic acid: Nonsteroidal anti-inflammatory drugs with low gastric ulcerogenic activity

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